(R)-(5'Z,4''E)-2-[5'-(5'',9''-dimethyldeca-4'',8''-dienylidene)tetrahydropyran-2'-yl]prop-2-en-1-ol | 337971-41-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-(5'Z,4''E)-2-[5'-(5'',9''-dimethyldeca-4'',8''-dienylidene)tetrahydropyran-2'-yl]prop-2-en-1-ol
• CAS: 337971-41-2
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: PETUFMRFERSDEK-HMFSFMJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.11
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-(5'Z,4''E)-2-[5'-(5'',9''-dimethyldeca-4'',8''-dienylidene)tetrahydropyran-2'-yl]prop-2-en-1-ol 在 manganese(IV) oxide 作用下， 以 正己烷 为溶剂， 反应 14.0h， 以70%的产率得到(R)-(5'Z,4''E)-2-[5'-(5'',9''-dimethyldeca-4'',8''-dienylidene)tetrahydropyran-2'-yl]propenal
  参考文献：
  名称：

  Enantioselective total synthesis and absolute stereostructure of hippospongic acid A

  摘要：

  A compound having the structure proposed for hippospongic acid A, a triterpene that specifically inhibits gastrulation of starfish embryos, was synthesized enantioselectively. The synthetic compound was not identical to the natural product. Comparison of the NMR spectra of the natural and synthetic compounds led us to propose an alternative structure, which was confirmed by enantioselective synthesis. The present synthesis established that the natural product has the (R)-configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01129-7
• 作为产物：
  描述：

  (R)-(Z)-{2-[5-(2-chloroethylidene)tetrahydropyran-2-yl]allyloxy}triisopropylsilane 在 三乙烯二胺 、 正丁基锂 、 四丁基氟化铵 、 sodium 作用下， 以 四氢呋喃 、 正己烷 、 正丁醇 为溶剂， 反应 2.75h， 生成 (R)-(5'Z,4''E)-2-[5'-(5'',9''-dimethyldeca-4'',8''-dienylidene)tetrahydropyran-2'-yl]prop-2-en-1-ol
  参考文献：
  名称：

  Enantioselective total synthesis and absolute stereostructure of hippospongic acid A

  摘要：

  A compound having the structure proposed for hippospongic acid A, a triterpene that specifically inhibits gastrulation of starfish embryos, was synthesized enantioselectively. The synthetic compound was not identical to the natural product. Comparison of the NMR spectra of the natural and synthetic compounds led us to propose an alternative structure, which was confirmed by enantioselective synthesis. The present synthesis established that the natural product has the (R)-configuration. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01129-7